


The First Performance

by destielinfinity4



Series: Kinktober [6]
Category: (Torchwood is very minor I warned you), Supernatural, Torchwood
Genre: Anal Sex, Beta Wanted, Bottom Dean Winchester, Condoms, Dean wears panties, Dom Jack Harkness, Established Relationship, Kinktober, Kinktober 2017, LGBT+ Characters, M/M, Masturbation, Mostly porn, Not Beta Read, Orders, Orgasm Control, Slight rubber kink, Some plot if you squint, Third person past tense, Top Castiel, Top Castiel/Bottom Dean Winchester, Webcam/Video Chat Sex, Wordcount: 1.000-5.000
Language: English
Status: Completed
Published: 2017-10-08
Updated: 2017-10-08
Packaged: 2019-01-10 12:28:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,068
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12299268
Author URL: https://archiveofourown.org/users/destielinfinity4/pseuds/destielinfinity4
Summary: Dean and Cas are going to fuck on a webcam for a dom on the internet who orders them around and wants them to put on a show.Dean isn't sure he's going to like it.





	The First Performance

**Author's Note:**

> Updated: October 7, 2017
> 
> Comment Modding is on so if someone suggests an edit for a typo or something I can fix it and not have the comment there forever.
> 
> Beta Request is for a second pair of eyes, I've edited this I promise

Dean looked at Cas lovingly as they worked together to tidy their room.  
"Are you sure you're ready for this Cas?"  
"Of course Dean! We've discussed the situation thoroughly, we've done the background check and the technological tests, and we still have plenty of time to shower before the appointment."  
Dean nodded. Truth be told, even though he was the one who'd pushed this, the one who'd been the most vocal about how hot and how fun it would be, Dean wasn't sure he was completely ready himself. He knew Cas could see it too. The bastard always saw straight through his false bravado. 'One of the few times he thinks anything straight' Dean thought to himself with a chuckle.  
Dean adjusted the pillows on their bed and started up the computer to test the connections again. It seemed they were finally ready. All that was left to do was shower and put a big anti-moose sock on the door.  
Cas and Dean showered together. They washed their hair, Dean shaved his legs because he did that sometimes, it wasn't weird. Guys can totally shave their legs if they want to. They both shaved their armpits. Next, they cleaned themselves out and washed all over with a nice smelling body wash. It wouldn't matter really because you can't see how someone smells through a webcam but it didn't matter, it was still worth doing.  
Once they'd finished showering Dean put on his favorite pair of panties, black lacy boyshorts and Cas squeezed into his BDSM pants. In Dean's opinion, nothing he'd ever spent money on was more worth it. Well except Baby, but hey, she and those shorts had a lot in common. They were black, shiny, and sexy as fuck. They were booty shorts, crotchless and they showed off Cas' dick perfectly, that and they made his ass look like heaven.  
Dean was getting hard just thinking about it. He tried to breathe, he didn't want to get the panties dirty yet, and there was plenty of time to stare at Cas' plump shiny ass during the scene. If he was allowed to that is.  
Next, they put on their regular clothes, Cas put on Dean's Ramones shirt which he'd permanently stollen, and a pair of dark-wash jeans. Dean wore a tight black T-shirt and light wash jeans. Most of the clothes Cas wore used to be Deans. It seemed that being on the planet for under ten years didn't usually leave the person with a very big or developed wardrobe. Jack had commented on it from the beginning when they'd first been sending pics. He said they dressed exactly the same and honesty Dean had never thought of it before.  
Cas set booted up the computer and opened Skype before looking at Dean with an expression of nervous excitement. Dean knew how Cas felt because he felt the same. It was new and exciting, and edgy, and it was going to be so much fun, but it was still so new. Dean hadn't felt that way in a while, it was kind of a rush.  
Ten minutes. They were pretty much ready but they knew He was busy until 9:00 so they had to wait.  
Dean put his arm around Cas and rubbed his back reassuringly, which caused Cas to turn and smile at him gratefully.  
"Would making out make you less nervous?" Dean leaned in closer to Cas, smirking.  
Cas smiled "Well, it's certainly worth a try. He didn't say it was against the rules." So Cas stood up and walked over to Dean, hands wrapping around his waist as he leaned in to kiss his boyfriend.  
They were interrupted by the sound of a skype call from their computer and they both pulled apart, looking each other in the eye before quickly moving to the computer to answer the call.  
When they answered they could see his face, He had black shiny hair, a clef in his chin, flirty eyes, and suspenders. The man smiled when he saw them through the camera.  
"Wow, you two are even more delectable in moving pictures than regular pictures! Oh, but I don't know what your voices sound like!" Suddenly his voice changed.  
All of the sweetness and flirtiness left, leaving a cold and firm tone. "Boys, introduce yourself to me. I want your name, your height, and a 'thank you, Master'. We'll start with bow-legs over here."

Dean realized that must be him. "Oh, uh, I'm Dean." Dean could feel his voice lowering with arousal "I'm 6'1, and uh," He paused, wanting to sound sincere "Thank you Master"

Dean listened to Cas as he introduced himself, his introduction was certainly more put-together than Dean's but hey, they were different kinds of guys and if He had a problem with it, there was no doubt in Dean's mind that he'd voice the concern. So it was fine, nothing to be worried about. If Jack did mind, Dean would just end up being spanked more or something, which he honestly didn't mind.

"Good, very good," Jack said quietly. "Now, please remove your shirts and pants. Are you wearing what I ordered you to?"

"Yes Sir" Both Dean and Cas answered in unison

"Good, get going."

And so they did, Removing their shirts and pants and setting them aside before presenting themselves to Jack."

Dean could feel Jack's eyes on his body, looking at him like a toy, sizing him up. He was starting to get hard already.

"Very good boys, very good. Now kiss each other, run your hands on each other's bodies like it's the first time you've done it."

Dean smiled at Cas again, this order wasn't hard, he tried his best to do it every time he was with Cas but no one needed to know that.

He approached Cas and put his hands on Cas' hips. Then he closed the distance between their bodies, pressing them together as he moved in for the kiss. Cas' hands came up and one held his shoulder as the other cupped his jawline. They made out slowly. Dean tried to move his hands together with their rhythm, slowly land gently. He was trying to be good, to follow Jack's orders like a good sub. It felt pretty good too, performing for Jack. It was like he was high, every touch was more intense, more surreal. Everything was better.

"Alright. Good. That's enough. Dean, show off Castiel for me."

Cas looked a bit nervous about being shown off, but Dean squeezed his hand briefly and he looked reassured.

Dean positioned Cas in front of the camera and sat him down on the bed. He crouched behind Cas and grabbed his chest roughly, and then he pinched Cas' nipples, making him hiss. Then he grabbed Cas' hair and pulled his neck back, before proceeding to kiss the skin and take his earlobe between his teeth. Then he ran his hands along the top of Cas' thighs, which caused him to push his legs open wider, showing off the crotchless shorts perfectly.

Jack moaned through the camera "Perfect Dean, just perfect. Switch places."

And so they did Cas turned Dean towards the camera and made a show of grabbing Dean's package, which made Dean whimper audibly. Then he raked his fingernails down Dean's chest and abs. Then he turned Dean around, looked straight at the camera and smacked his ass hard, making Dean bite his lip and then smile, he then reached up between Deans legs and snuck a hand in, about to stroke Dean.

"No! Not yet Castiel, slap his ass some more, how about..." He thought for a moment "Ten more."

Dean stuck his lacy boyshorts covered ass into the air ready to take the hits from Cas and eager to please Jack.

And Cas delivered. He spanked Dean ten more times, five on one side five on the other. Dean loved the clean smacking sound the Cas' palm made on his ass there was something about it that was just, awesome.

"Very good boys." Jack's voice came through the speaker "Now, I have a question for you. Who usually tops, and who usually bottoms."

"I uh, I -I bottom usually." Dean stammered, he was never much good at talking when he was turned on.

"What's that Dean? Don't mutter."

Dean cleared his throat, "I usually bottom, Sir."

"Alright Dean, I want you to bottom today. I want to see your energy as a couple."

Cas looked at Dean lovingly before going to the bedside table for lube and a condom.

Dean looked over his shoulder at the camera and winked at Jack before pulling the panties over his ass. Cas walked back towards Dean while putting lube on three fingers. He started with one, circling Dean's hole slowly and sensually, just around the edges. Then he finally brought his finger across Dean's hole and Dean whimpered.

Dean wanted to be filled up right then and there, he didn't want the process drawn out. But Cas took his time anyway. Taking his time with one finger before adding another, and once he'd gotten all three in he was careful, making sure Dean was ready.

Finally, Cas pulled his fingers out and put the condom and some more lube on his dick.

Dean closed his eyes, waiting to feel Cas push into him, but he didn't feel anything. He opened his eyes and looked over his shoulder. Cas was looking at Jack, waiting for his command

"Yes Castiel, you may."

Then finally Cas pushed inside Dean, slowly and gently. He pulled in and out a few times before he increased his pace, putting his hands on Dean's hips. Dean closed his eyes and his head kept rolling back and forth. Eventually, the pace really picked up and Dean could tell Cas was getting close to the edge. Cas finally came inside Dean with a series of loud moans. Cas pulled out and tossed the condom in the trash and grabbed the nearby towel, placing it on the bed so that Dean could sit without getting the bed covered in lube. As Dean went to sit, Cas reached out to caress Dean's leg.

Dean looked at Jack expectantly, wondering how, or if, he was going to get to come.

After what felt like a very long time, Jack finally cleared his throat and spoke "Dean. I want you to finish yourself, but you may not come until I give you permission."

Dean didn't need to be told twice, he took his cock in his hand and began stroking, slowly at first to get used to the sensation, but his pace quickly sped up as he neared orgasm. Cas was sitting next to him, clearly torn between sitting back to watch, and putting his hands on Dean himself. Dean couldn't really tell what Jack was doing since it was on skype and the camera was only trained on his face.

Dean could feel himself getting close, he didn't want to break Jack's rule, he could wait a bit longer. Dean moaned and quickened his pace even more. Finally, it was time.

"Jack! Can I come?" Dean could hear the desperation in his voice.

"Hmm." Jack was teasing him, of course.

Finally, Jack smiled "Yes Dean, you may come."

And with that, a few strokes later Dean came.

When he'd caught his breath Jack addressed both of them. "Well boys, it was so nice to meet both of you! I'd love to dom you in the future and possibly do some more, adventurous things."

Dean and Cas smiled at each other quickly before looking back at the camera.

"Well I've got to go now, I'll be in contact shortly." and with that, the call disconnected.

Dean let himself fall back on the bed, saying "God I love being ordered around. That was fucking hot."

"Agreed." Cas smiled at him and took his hand. "However, I really need to get out of these shorts."

"Oh god" Dean laughed rubber shorts may be sexy as fuck, but they're not the most comfortable. "Well hurry up I wanna kiss you some more."

Cas smiled and made quick work of taking off the shorts before joining Dean on the bed.

"We should do this again sometime huh Cas?"

"Definitely."

Dean snuggled up to Cas and closed his eyes. He was glad they’d done that. It was Awesome.

**Author's Note:**

> Comments and Kudos make me very happy. I think I‘d actually cry if someone made fanart of my work. Like for real. If you post anywhere about it use my archive name as the hashtag or tag me. Follow my Tumblr for updates! Feel free to message me with prompts and ideas. If you want to beta any of my works message me on Tumblr. Check out my other works!!! (Ily)


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